1,3-Dipolar Cycloaddition on
Baylis-Hillman Adducts: Novel Synthesis of Pyrrolidines,
Spiropyrrolidines, and Spiropyrrolizidines

Manickam Bakthadoss; Nagappan Sivakumar; Anthonisamy Devaraj; Duddu S. Sharada

doi:10.1055/s-0030-1260053

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Synthesis 2011(13): 2136-2146
DOI: 10.1055/s-0030-1260053

PAPER

1,3-Dipolar Cycloaddition on Baylis-Hillman Adducts: Novel Synthesis of Pyrrolidines, Spiropyrrolidines, and Spiropyrrolizidines

Manickam Bakthadoss*^a, Nagappan Sivakumar^a, Anthonisamy Devaraj^a, Duddu S. Sharada^b
^a Dept. of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Fax: +91(44)22352494; e-Mail: bhakthadoss@yahoo.com;
^b Organic Chemistry Division, Central Leather Research Institute, Adyar, Chennai 600 020, Tamil Nadu, India

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Publikationsverlauf

Received 12 February 2011
Publikationsdatum:
19. Mai 2011 (online)

Abstract
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Abstract

A facile regio- and stereoselective synthesis of functionalized pyrrolidines, spiropyrrolidines, and spiropyrrolizidines using the Baylis-Hillman adducts derived from nitroolefins via intermolecular [3+2]-cycloaddition reaction is reported.

Key words

Baylis-Hillman reaction - intermolecular [3+2] cycloaddition - azomethine ylides - 1,3-dipolar cycloaddition - pyrrolidines - spiro compounds

References

1 Basavaiah D. Reddy BS. Badsara BS. Chem. Rev. 2010, 110: 5447

Suche in Google Scholar
2a Declerck V. Martinez J. Lamaty F. Chem. Rev. 2009, 109: 1

Suche in Google Scholar
2b Singh V. Batra S. Tetrahedron 2008, 64: 4511

Suche in Google Scholar
2c Basavaiah D. Rao KV. Reddy RJ. Chem. Soc. Rev. 2007, 36: 1581

Suche in Google Scholar
2d Masson G. Housseman C. Zhu J. Angew. Chem. Int. Ed. 2007, 46: 4614

Suche in Google Scholar
2e Basavaiah D. Rao AJ. Satyanarayana T. Chem. Rev. 2003, 103: 811

Suche in Google Scholar
2f Ciganek E. Org. React. 1997, 51: 201

Suche in Google Scholar
2g Auvray P. Knochel P. Normant JF. Tetrahedron Lett. 1986, 27: 5095

Suche in Google Scholar
2h Prasad BAS. Knochel P. Tetrahedron 1997, 53: 16711

Suche in Google Scholar
2i Basavaiah D. Rao PD. Hyma RS. Tetrahedron 1996, 52: 8001

Suche in Google Scholar
2j Drewes SE. Roos GHP. Tetrahedron 1988, 44: 4653

Suche in Google Scholar
3a Ma GN. Jiang JJ. Shi M. Wei Y. Chem. Commun. 2009, 5496
3b Amarante GW. Milagre HM. Vaz SBG. Ferreira BRV. Eberlin MN. Coelho F. J. Org. Chem. 2009, 74: 3031

Suche in Google Scholar
3c Trofimov A. Gevorgyan V. Org. Lett. 2009, 11: 253

Suche in Google Scholar
3d Deb I. Shanbhag P. Mobin SM. Namboothiri INN. Eur. J. Org. Chem. 2009, 4091
3e Krafft ME. Haxell TFN. Seibert KA. Abboud KA. J. Am. Chem. Soc. 2006, 128: 4174

Suche in Google Scholar
3f Turki T. Villieras J. Amri H. Tetrahedron Lett. 2005, 46: 3071

Suche in Google Scholar
3g Back TG. Rankic DA. Sorbetti JM. Wulff JE. Org. Lett. 2005, 7: 2377

Suche in Google Scholar
3h Nair V. Abhilash KG. Synthesis 2005, 1967
3i Jellerichs BG. Kong JR. Krische MJ. J. Am. Chem. Soc. 2003, 125: 7758

Suche in Google Scholar
3j Basavaiah D. Sreenivasalu B. Rao AJ. J. Org. Chem. 2003, 68: 5983

Suche in Google Scholar
3k Basavaiah D. Bakthadoss M. Jayapal Reddy G. Synthesis 2001, 919
3l Li G. Gao J. Wei HX. Enright M. Org. Lett. 2000, 2: 617

Suche in Google Scholar
3m Yang KS. Chen K. Org. Lett. 2000, 2: 729

Suche in Google Scholar
3n Basavaiah D. Gowriswari VVL. Bharathi TK. Tetrahedron Lett. 1987, 28: 4591

Suche in Google Scholar
3o Amri H. Villieras J. Tetrahedron Lett. 1986, 27: 4307

Suche in Google Scholar
4a Gendrineau T. Demoulin N. Navarre L. Genet J.-P. Darses S. Chem. Eur. J. 2009, 15: 4710

Suche in Google Scholar
4b Yadav LDS. Awasthi C. Tetrahedron Lett. 2009, 50: 3801

Suche in Google Scholar
4c Singh V. Batra S. Eur. J. Org. Chem. 2008, 5446
4d Shafiq Z. Liu L. Liu Z. Wang D. Chen YJ. Org. Lett. 2007, 9: 2525

Suche in Google Scholar
4e Lee SI. Hwang GS. Shin SC. Lee TG. Jo RH. Ryu DH. Org. Lett. 2007, 9: 5087

Suche in Google Scholar
4f Gowrisankar S. Lee KY. Lee CG. Kim JN. Tetrahedron Lett. 2004, 45: 6141

Suche in Google Scholar
4g Kabalka GW. Venkataiah B. Dong G. J. Org. Chem. 2004, 69: 5807

Suche in Google Scholar
4h Basavaiah D. Reddy RM. Tetrahedron Lett. 2001, 42: 3025

Suche in Google Scholar
4i Basavaiah D. Sarma PKS. J. Chem. Soc., Chem. Commun. 1992, 955
4j Bode ML. Kaye PT.
J. Chem. Soc., Perkin Trans. 1 1990, 2612
5 Zeni G. Larock RC. Chem. Rev. 2006, 106: 4644

Crossref PubMed Suche in Google Scholar
6 Basavaiah D. Roy S. Org. Lett. 2008, 10: 1819

Crossref Suche in Google Scholar
7 Savitha G. Niveditha SK. Muralidharan D. Perumal PT. Tetrahedron Lett. 2007, 48: 2943

Crossref Suche in Google Scholar
8a Muthusamy S. Gunanathan C. Babu SA. Tetrahedron Lett. 2001, 42: 523

Suche in Google Scholar
8b Shanmugam P. Viswambharan B. Madhavan S. Org. Lett. 2007, 9: 4095

Suche in Google Scholar
9a Lown JW. In 1,3-Dipolar Cycloaddition Chemistry Vol. 1: Padwa A. Wiley; New York: 1984. p.2

Suche in Google Scholar
9b Najera C. Sansano JM. Angew. Chem. Int. Ed. 2005, 44: 6272

Suche in Google Scholar
9c Gothelf KV. In Cycloaddition Reactions in Organic Synthesis Kobayashi S. Jørgensen KA. Wiley-VCH; Weinheim: 2002. p.211
9d Gothelf KV. Jørgensen KA. Chem. Rev. 1998, 98: 863

Suche in Google Scholar
10a Cordell GA. The Alkaloids: Chemistry and Biology Academic Press; San Diego: 1998.
10b Cui C.-B. Kakeya H. Osada H. Tetrahedron 1996, 52: 12651

Suche in Google Scholar
10c Xue J. Zhang Y. Wang X.-I. Fun HK. Xu JH. Org. Lett. 2000, 2: 2583

Suche in Google Scholar
10d Klumpp DA. Yeung KY. Prakash GKS. Olah GA. J. Org. Chem. 1998, 63: 4481

Suche in Google Scholar
11a Jossang A. Jossang P. Hadi HA. Sevenet T. Bodo B. J. Org. Chem. 1991, 56: 6527

Suche in Google Scholar
11b Wong WH. Lim PB. Chuah CH. Phytochemistry 1996, 41: 313

Suche in Google Scholar
11c Dideberg O. Lamotte-Brasseur J. Dupont L. Campsteyn H. Vermeire M. Angenot L. Acta Crystallogr., Sect. B 1977, 33: 1796

Suche in Google Scholar
11d Cui CB. Kakeya H. Okada G. Onose R. Osada H. J. Antibiot. 1996, 49: 527

Suche in Google Scholar
11e Bindra JS. The Alkaloids Vol. 14: Manske RHF. Academic Press; New York: 1973. p.84

Suche in Google Scholar
11f Lin H. Danishefky S. Angew. Chem. Int. Ed. 2003, 42: 36

Suche in Google Scholar
12a Fejes I. Toke L. Blasko G. Nyerges M. Pak CS. Tetrahedron 2000, 56: 8545

Suche in Google Scholar
12b Nyerges M. Bitter I. Kadas I. Toth G. Toke L. Tetrahedron 1995, 51: 11489

Suche in Google Scholar
12c Rang HP. Dale MM. Pharmacology Churchill Livingstone; Edinburgh: 1991.
12d Song C. Leonard BE. Fundamentals of Psychoneuroimmunology John Wiley; Chichester: 2000.
12e Albert A. Selective Toxicity Chapman and Hall; London: 1985.
13a De Amici M. De Michelli C. Sani VM. Tetrahedron 1990, 46: 1975

Suche in Google Scholar
13b Early WG. Oh T. Overman LE. Tetrahedron Lett. 1988, 29: 3785

Suche in Google Scholar
13c Kozikowski AP. Acc. Chem. Res. 1984, 17: 410

Suche in Google Scholar
13d Ban Y. Taga N. Oishi T. Chem. Pharm. Bull. 1976, 24: 736

Suche in Google Scholar
13e Van Tamlen EE. Yardley JP. Miyano M. Hinshaw WB. J. Am. Chem. Soc. 1969, 91: 7333

Suche in Google Scholar
13f Howe RK. Shelton BR. J. Org. Chem. 1990, 55: 4603

Suche in Google Scholar
13g Cohan VL, and Kleinman EE. inventors; WO 9,524,398. ; Chem. Abstr. 1995, 122, 20667j
13h Ban Y. Seto M. Oishi T. Chem. Pharm. Bull. 1975, 23: 2605

Suche in Google Scholar
13i Ban Y. Taga N. Oishi T. Tetrahedron Lett. 1974, 15: 187

Suche in Google Scholar
13j Caroll WA. Grieco PA. J. Am. Chem. Soc. 1993, 115: 1164

Suche in Google Scholar
14 Ding K. Lu Y. Nikolovska-Coleska Z. Wang G. Qiu S. Shangary S. Gao W. Qin D. Stuckey J. Krajewski K. Roller PP. Wang S. J. Med. Chem. 2006, 49: 3432

Crossref PubMed Suche in Google Scholar
15a Hilton ST. Ho TCT. Pljevaljcic G. Jones K. Org. Lett. 2000, 2: 2639

Suche in Google Scholar
15b Coldham I. Hufton R. Chem. Rev. 2005, 105: 2765

Suche in Google Scholar
15c Pandey G. Banerjee P. Gadre SR. Chem. Rev. 2006, 106: 4484

Suche in Google Scholar
16a Daly JW. Spande TWF. Whittaker N. Highet RJ. Feigl D. Nishimori T. Tokuyama T. Myers CW.
J. Nat. Prod. 1986, 49: 265

Suche in Google Scholar
16b Hilton ST. Ho TCT. Pljevaljcic G. Jones K. Org. Lett. 2000, 2: 2639

Suche in Google Scholar
16c Liddell JR. Nat. Prod. Rep. 1996, 13: 187

Suche in Google Scholar
16d Liddell JR. Nat. Prod. Rep. 1997, 14: 653

Suche in Google Scholar
16e Marti C. Carreira EM. Eur. J. Org. Chem. 2003, 2209
16f Toyota M. Ihara M. Nat. Prod. Rep. 1998, 15: 327

Suche in Google Scholar
16g Dounary AB. Hatanaka K. Kodanko JJ. Oestreich M. Pfeifer LA. Weiss MM. J. Am. Chem. Soc. 2003, 125: 6261 ; and references therein

Suche in Google Scholar
17a Baylis AB, and Hillman MED. inventors; DE 2,155,113. ; Chem. Abstr. 1972, 77, 34174q
17b Rastogi N. Namboothiri INN. Cojocaru M. Tetrahedron Lett. 2004, 45: 4745

Suche in Google Scholar
18a Bakthadoss M. Sivakumar G. Kannan D. Org. Lett. 2009, 11: 4466

Suche in Google Scholar
18b Bakthadoss M. Murugan G. Eur. J. Org. Chem. 2010, 5825
18c Bakthadoss M. Sivakumar N. Devaraj A. Synthesis 2011, 611
18d Bakthadoss M. Sivakumar N. Synlett 2009, 1014
18e Bakthadoss M. Sivakumar N. Sivakumar G. Murugan G. Tetrahedron Lett. 2008, 49: 820

Suche in Google Scholar
18f Bakthadoss M. Murugan G. Synth. Commun. 2008, 38: 3406

Suche in Google Scholar
18g Bakthadoss M. Murugan G. Synth. Commun. 2009, 39: 1290

Suche in Google Scholar

19

The X-ray crystal structure data of 8d, 9a, 10d, and 11a have been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition numbers CCDC 812105 (8d), 676397 (9a), 676668 (10d), and 812104 (11a).